Everyone will tell you to move to Florida or Texas to retire tax-free. But the truth? Taxes are more complicated than a “No State Income Tax” billboard. In this first part of a two-part series, we unpack The Great Tax Mirage and reveal why some so-called high-tax states like New Jersey, Pennsylvania, and Iowa may leave retirees with more money in their pocket than the sunny paradises they’re fleeing.

We dive into Fidelity’s latest study modeling retirees withdrawing $100,000 a year from an IRA and show how effective tax rates—what you actually pay after exemptions and deductions—can dramatically flip conventional wisdom on its head. For example, a couple retiring in Oregon might pay close to 13% in effective taxes, while a move to Iowa could drop that number to 7.5%, potentially growing tens of thousands of dollars over a decade.

We also explore the underrated power of marriage in retirement planning. Married couples filing jointly can save around six percentage points on combined federal and state taxes versus singles—enough to add tens of thousands of dollars to a nest egg over ten years.

Key takeaways from this episode include:

• No state income tax doesn’t automatically mean you keep more money.
  
  
• Certain high-tax states offer exemptions and deductions that outperform so-called tax havens.
  
  
• Marriage can be one of the most powerful retirement tax strategies.
  
  
• Your effective tax rate—not the headline rate—determines what you actually keep.
  
  
• Planning where to retire is about life satisfaction as much as taxes.
  
  

Whether you’re dreaming of beaches, cornfields, or just a comfortable, worry-free retirement, this episode will change the way you think about where your money—and your life—goes next.

Part Two drops next week, where we’ll rank the best and worst states for retirees, explore the real impact of marital magic, and dig into other often-overlooked factors that matter more than taxes when choosing where to spend your golden years.

If you enjoy the show, please leave a review on Apple Podcasts or Spotify and share it with a friend who’s plotting their retirement escape. It helps more than you know—and makes sure that no one accidentally retires somewhere that quietly nibbles their nest egg.

This is part two of our financial order of operations series.

In part one, we covered the non-negotiables—the oxygen mask, debt payoff, insurance, and the foundation of every real financial plan. This week, we get into the gray areas. The places where conventional wisdom isn’t just outdated—it’s expensive.

Here’s what we cover:

7️⃣ The Emergency Fund Myth
You’ve heard it before: “Keep six months of expenses in cash.” The problem? That advice was built for a world where savings accounts paid double-digit interest. Today, it’s fear-based and mathematically backward. Most people will go years without a true financial emergency, and keeping $20,000 in cash for a maybe costs far more than it saves. Learn how to balance liquidity with growth without putting your future on pause.

8️⃣ The Taxable Brokerage Account Advantage
Once you’ve maxed your Roth IRA, captured your 401(k) match, and funded your HSA, it’s time to open a taxable brokerage account. This is your flexibility play—your bridge between today and retirement. Access your money anytime, invest in low-cost index funds, and take advantage of long-term capital gains rates that beat most income taxes.

9️⃣ The Right Way to Think About Debt
Debt isn’t moral—it’s mathematical. If your rate is above 5%, pay it off first. If it’s below 5%, investing probably wins over time. But if it’s keeping you up at night, pay it off anyway. Personal finance is personal—and peace of mind compounds, too.

🎯 Bonus: The 20-Minute “Tiered Pricing” Hack
Call your phone, internet, and streaming companies once a year. Tell them you’re considering canceling. Decline their first “special offer,” and watch the discounts appear. It’s the modern coupon—no scissors required—and it can save you $1,000+ a year to redirect into your investments.

At the end of the day, this two-part series gives you a complete, math-first roadmap for building wealth that lasts. It works whether you’re starting out or managing seven figures.

And if you're interested in learning more about this week's show sponsor, Facet, check out facet.com/tyler today to learn more!

🎧 Listen now wherever you get your podcasts.

💌 Join the newsletter for weekly financial clarity (and the occasional heretical take): https://socialcapconnect.substack.com/subscribe

This week we’re tearing apart one of personal finance’s most overused frameworks: the “financial order of operations.”

You’ve heard a version of it before—pay this, save that, sacrifice now, maybe retire someday. The problem? Most of those systems were built by people who either (a) never had real financial stress, or (b) have spent too long in the Dave Ramsey cinematic universe.

So, I rebuilt the order from scratch. And it actually works in the real world, whether you make $40,000 or $400,000.

Here’s what we cover:

1️⃣ Put your own oxygen mask on first.
Take care of yourself before your kids. Financial stability isn’t selfish—it’s responsible.

2️⃣ Obliterate credit card debt.
The “snowball method” is financial astrology. Attack the highest-interest balance first.

3️⃣ Get insurance.
If someone depends on your income, you need term life and long-term disability. No gimmicks.

4️⃣ Max out your Roth IRA.
It’s flexible, tax-free, and doubles as a stealth emergency fund.

5️⃣ Grab your 401(k) match.
A 50% employer match is the only free lunch on Wall Street.

6️⃣ Max out your HSA (if you can).
The triple tax advantage—deductible going in, tax-free growth, tax-free withdrawals—is unbeatable.

We’ll go deeper into emergency funds, taxable brokerage accounts, and smart debt strategies in Part 2 next week.

And a MASSIVE thank you to this episode's sponsor, Facet. If you are tired of paying more to an advisor simply because you make more, check out facet.com/tyler today to learn more.

👉 PLUS: stick around until the end of the episode for a modern trick that helps you find the money to do all of this in under 20 minutes—without canceling Netflix or giving up your morning coffee.

If this episode helps you—or if you simply enjoy hearing someone roast bad financial advice with love—please consider leaving a review on Apple or Spotify or share this with a friend who still believes paying off a $200 credit card before a $20,000 one is “confidence building.”

🎧 Listen now wherever you get your podcasts.

📩 Join my newsletter for weekly financial philosophy that treats you like an adult: https://socialcapconnect.substack.com/subscribe